Np mrd loader

Showing NP-Card for Trimethyl phosphonoacetate (NP0002635)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2020-11-23 18:25:44 UTC
Updated at2021-08-12 19:51:42 UTC
NP-MRD IDNP0002635
Secondary Accession NumbersNone
Natural Product Identification
Common NameTrimethyl phosphonoacetate
Provided ByBMRBBMRB logo
Description It was first documented in 2002 (PMID: 26389497). Based on a literature review very few articles have been published on methyl 2-(dimethoxyphosphoryl)acetate (PMID: 17984079) (PMID: 26389486) (PMID: 26389480) (PMID: 26389479).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002635 (Trimethyl phosphonoacetate)


     RDKit          2D

 22 21  0  0  0  0  0  0  0  0999 V2000
   -4.3352    0.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729    0.4336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8524   -0.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940   -2.0992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3901   -0.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722    0.0028    0.0000 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.5345    0.3370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7380    1.4651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8373    2.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4065   -1.4595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8399   -1.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6695    1.5617    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0010   -1.3629    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7975   -0.2349    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7243    1.1309    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0558   -1.7937    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8167    3.5849    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.3864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9365    3.5063    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3983   -3.3347    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2816   -0.4677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2734   -2.3429    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  6
  8  9  1  0
  6 10  1  0
 10 11  1  0
  1 12  1  6
  1 13  1  0
  1 14  1  0
  5 15  1  1
  5 16  1  0
  9 17  1  6
  9 18  1  0
  9 19  1  0
 11 20  1  6
 11 21  1  0
 11 22  1  0
M  END
Download

3D MOL for NP0002635 (Trimethyl phosphonoacetate)

NP0002635
     RDKit          3D

 22 21  0  0  0  0  0  0  0  0999 V2000
    4.0557   -0.7211    0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9066    0.0551    0.4451 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363   -0.3037    0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5098   -1.3688   -0.6082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4700    0.5825    0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0623   -0.0937   -0.2608 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.8132   -0.5786   -1.6834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2382    1.1175   -0.2312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7212    2.3303    0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6302   -1.3943    0.6224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8923   -1.7371    0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8078   -0.4543    0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8435   -1.8139    0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.4619   -0.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4585    0.7040    1.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623    1.5450   -0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5309    2.9562    0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2049    2.8960   -0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9789    2.1778    1.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8502   -2.5802   -0.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3371   -0.8600   -0.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6061   -1.9965    0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  5 15  1  0
  5 16  1  0
  9 17  1  0
  9 18  1  0
  9 19  1  0
 11 20  1  0
 11 21  1  0
 11 22  1  0
M  END
Download

3D SDF for NP0002635 (Trimethyl phosphonoacetate)


     RDKit          2D

 22 21  0  0  0  0  0  0  0  0999 V2000
   -4.3352    0.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729    0.4336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8524   -0.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940   -2.0992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3901   -0.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722    0.0028    0.0000 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.5345    0.3370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7380    1.4651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8373    2.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4065   -1.4595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8399   -1.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6695    1.5617    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0010   -1.3629    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7975   -0.2349    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7243    1.1309    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0558   -1.7937    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8167    3.5849    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.3864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9365    3.5063    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3983   -3.3347    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2816   -0.4677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2734   -2.3429    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  6
  8  9  1  0
  6 10  1  0
 10 11  1  0
  1 12  1  6
  1 13  1  0
  1 14  1  0
  5 15  1  1
  5 16  1  0
  9 17  1  6
  9 18  1  0
  9 19  1  0
 11 20  1  6
 11 21  1  0
 11 22  1  0
M  END
> <DATABASE_ID>
NP0002635

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CP(=O)(OC)OC

> <INCHI_IDENTIFIER>
InChI=1S/C5H11O5P/c1-8-5(6)4-11(7,9-2)10-3/h4H2,1-3H3

> <INCHI_KEY>
SIGOIUCRXKUEIG-UHFFFAOYSA-N

> <FORMULA>
C5H11O5P

> <MOLECULAR_WEIGHT>
182.112

> <EXACT_MASS>
182.034410452

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.68675284124529

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-(dimethyl phosphono)acetate

> <ALOGPS_LOGP>
-0.62

> <JCHEM_LOGP>
-0.42275943466666677

> <ALOGPS_LOGS>
-0.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.555301349758917

> <JCHEM_PKA_STRONGEST_BASIC>
-7.124877387572477

> <JCHEM_POLAR_SURFACE_AREA>
61.83000000000001

> <JCHEM_REFRACTIVITY>
37.3677

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.42e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (dimethyl phosphono)acetate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002635 (Trimethyl phosphonoacetate)

NP0002635
     RDKit          3D

 22 21  0  0  0  0  0  0  0  0999 V2000
    4.0557   -0.7211    0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9066    0.0551    0.4451 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363   -0.3037    0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5098   -1.3688   -0.6082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4700    0.5825    0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0623   -0.0937   -0.2608 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.8132   -0.5786   -1.6834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2382    1.1175   -0.2312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7212    2.3303    0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6302   -1.3943    0.6224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8923   -1.7371    0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8078   -0.4543    0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8435   -1.8139    0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.4619   -0.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4585    0.7040    1.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623    1.5450   -0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5309    2.9562    0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2049    2.8960   -0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9789    2.1778    1.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8502   -2.5802   -0.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3371   -0.8600   -0.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6061   -1.9965    0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  5 15  1  0
  5 16  1  0
  9 17  1  0
  9 18  1  0
  9 19  1  0
 11 20  1  0
 11 21  1  0
 11 22  1  0
M  END
Download

PDB for NP0002635 (Trimethyl phosphonoacetate)

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       5.541   5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.207   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.207   3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.874   3.850   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.644  -0.564   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.541   3.850   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.540   0.000   0.000  0.00  0.00           O+0
HETATM   11  P   UNK     0       2.874   0.770   0.000  0.00  0.00           P+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5   11                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5                                                            
CONECT    7   11                                                            
CONECT    8    1    5                                                       
CONECT    9    2   11                                                       
CONECT   10    3   11                                                       
CONECT   11    4    7    9   10                                             
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
Download

3D PDB for NP0002635 (Trimethyl phosphonoacetate)

COMPND    NP0002635
HETATM    1  C1  UNL     1       4.056  -0.721   0.169  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.907   0.055   0.445  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.636  -0.304   0.037  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.510  -1.369  -0.608  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.470   0.583   0.375  1.00  0.00           C  
HETATM    6  P1  UNL     1      -1.062  -0.094  -0.261  1.00  0.00           P  
HETATM    7  O3  UNL     1      -0.813  -0.579  -1.683  1.00  0.00           O  
HETATM    8  O4  UNL     1      -2.238   1.117  -0.231  1.00  0.00           O  
HETATM    9  C4  UNL     1      -1.721   2.330   0.215  1.00  0.00           C  
HETATM   10  O5  UNL     1      -1.630  -1.394   0.622  1.00  0.00           O  
HETATM   11  C5  UNL     1      -2.892  -1.737   0.128  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.808  -0.454   0.957  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.844  -1.814   0.200  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.515  -0.462  -0.800  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.459   0.704   1.472  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.662   1.545  -0.159  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.531   2.956   0.632  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.205   2.896  -0.574  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.979   2.178   1.037  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.850  -2.580  -0.593  1.00  0.00           H  
HETATM   21  H10 UNL     1      -3.337  -0.860  -0.397  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.606  -1.997   0.946  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   15   16
CONECT    6    7    7    8   10
CONECT    8    9
CONECT    9   17   18   19
CONECT   10   11
CONECT   11   20   21   22
END
Download

SMILES for NP0002635 (Trimethyl phosphonoacetate)

COC(=O)CP(=O)(OC)OC
Download

INCHI for NP0002635 (Trimethyl phosphonoacetate)

InChI=1S/C5H11O5P/c1-8-5(6)4-11(7,9-2)10-3/h4H2,1-3H3
Download
View in JSmol
Synonyms
ValueSource
Methyl 2-(dimethoxyphosphoryl)acetic acidGenerator
Trimethylacetyl phosphateMeSH
Trimethyl phosphonoacetic acidGenerator
Chemical FormulaC5H11O5P
Average Mass182.1120 Da
Monoisotopic Mass182.03441 Da
IUPAC Namemethyl 2-(dimethyl phosphono)acetate
Traditional Namemethyl (dimethyl phosphono)acetate
CAS Registry NumberNot Available
SMILES
COC(=O)CP(=O)(OC)OC
InChI Identifier
InChI=1S/C5H11O5P/c1-8-5(6)4-11(7,9-2)10-3/h4H2,1-3H3
InChI KeySIGOIUCRXKUEIG-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dialkyl alkylphosphonates. These are compounds containing a phosphonic acid that is diesterified with alkyl groups, and the phosphorus atom is also directly attached to an alkyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphonic acids and derivatives
Sub ClassPhosphonic acid diesters
Direct ParentDialkyl alkylphosphonates
Alternative Parents
Substituents
  • Dialkyl alkylphosphonate
  • Phosphonic acid ester
  • Methyl ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organophosphorus compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.62ALOGPS
logP-0.42ChemAxon
logS-0.73ALOGPS
pKa (Strongest Acidic)18.56ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area61.83 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.37 m³·mol⁻¹ChemAxon
Polarizability15.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID72283
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Authors unspecified: Lung Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389497 ]
  3. Authors unspecified: Endometrial Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:26389486 ]
  4. Authors unspecified: Ewing Sarcoma and Undifferentiated Small Round Cell Sarcomas of Bone and Soft Tissue Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389480 ]
  5. Authors unspecified: Bladder Cancer Treatment (PDQ(R)): Patient Version. 2002. [PubMed:26389479 ]